2-烯丙基-4-乙氧基苯酚 | 142875-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-烯丙基-4-乙氧基苯酚
• 英文名称: 2-allyl-4-ethoxyphenol
• 英文别名: 4-ethoxy-2-allyl-phenol；6-Hydroxy-3-aethoxy-1-allyl-benzol；Aethyl-(4-hydroxy-3-allyl-phenyl)-aether；4-Aethoxy-2-allyl-phenol；4-ethoxy-2-prop-2-enylphenol
• CAS: 142875-24-9
• 化学式: C₁₁H₁₄O₂
• mdl: MFCD05270920
• 分子量: 178.231
• InChiKey: MSNKNSRKIJBFMX-UHFFFAOYSA-N

物化性质

• 沸点：
  184-185 °C(Press: 50 Torr)
• 密度：
  1.057 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2909500000

反应信息

• 作为反应物：
  描述：

  2-烯丙基-4-乙氧基苯酚 在 臭氧 、 溶剂黄146 作用下， 生成 5-ethoxy-3H-benzofuran-2-one
  参考文献：
  名称：

  Ketene Acetals. XIV. The Reactions of Ketene Acetal with Quinones

  摘要：

  DOI：

  10.1021/ja01235a006
• 作为产物：
  描述：

  4-乙氧基苯酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 生成 2-烯丙基-4-乙氧基苯酚
  参考文献：
  名称：

  反对白菜弯角线虫Trichoplusia ni的二烷氧基苯和二烷氧基烯丙基苯的摄食和产卵抑制剂：潜在的昆虫行为控制剂

  摘要：

  在实验室生物测定中，针对白菜弯角曲霉Trichoplusia ni评估了各个二烷氧基苯化合物/对以及通过取代的烯丙氧基苯的克莱森重排获得的羟基或烷氧基取代的烯丙基苯的拒食剂，产卵抑制物和毒性作用。大多数化合物/组强烈抑制幼虫摄食，有些还表现出温和的毒性和产卵抑制作用。一些化合物/组比商业驱虫剂DEET（N，N- diethyl- m-甲苯胺），因为进食和产卵都可以阻止白菜弯角。根据获得的产卵数据，提出了有关产卵部位的一般假设：一种与苯环同一侧的烷基和烯丙基结合的方式会产生阻吓作用，另一种与烷基和烯丙基的结合方式相反。苯环导致刺激。结果表明，某些构效关系对提高化合物的功效和设计用于农业的新型无毒昆虫控制剂很有用。

  DOI：

  10.1021/jf9045123

文献信息

• Photoredox-Catalyzed Oxy-/Aminofluoroalkylative Cyclization of Alkenes
  作者：Jianhua Liao、Lu Ouyang、Yinlong Lai、Renshi Luo

  DOI：10.1021/acs.joc.0c00457

  日期：2020.4.17

  oxy-/aminofluoroalkylative cyclization of alkenes for coupling available Rf–I reagents to generate fluoroalkylated 2,3-dihydrobenzofuran and indolin derivatives with good to excellent yields under mild conditions. A wide range of functional groups are tolerated. The mechanistic investigation of radical trapping and cyclic voltammetry experiments proposed that a radical/SET (single electron transfer)

  在这里，我们描述了烯烃的光氧化还原催化的氧-/氨基氟烷基化环化反应，用于偶联可用的R f -I试剂，以在温和条件下以良好或优异的产率生成氟代烷基化的2,3-二氢苯并呋喃和吲哚衍生物。可以容忍各种各样的官能团。自由基捕获和循环伏安法实验的机理研究表明，在此反应中进行了自由基/ SET（单电子转移）途径。
• Spectroscopic and theoretical studies on intramolecular OH–π hydrogen bonding in 4-substituted 2-allylphenols
  作者：Paul Rademacher、Levan Khelashvili、Klaus Kowski

  DOI：10.1039/b504765j

  日期：——

  relationship between the strength of the intramolecular hydrogen bond, DeltaIP(C[double bond]C), Deltanu(OH) values and substituent constants it is established how substituents in 4-position affect the intramolecular OH-pi hydrogen bond. The investigations demonstrate that the DeltaIP(C[double bond]C) data can be used as descriptors for this intramolecular interaction.

  2-烯丙基苯酚（1）构成了构象异构体的混合物，其中可以区分OH-pi氢键封闭的（1a）和开放的形式（1b）。已经合成了4-取代的2-烯丙基苯酚（2-9），并通过理论和光谱方法进行了研究。在1-9中，氢键的能量和结构显示出随取代基的明显变化。在大多数化合物的PE光谱中，可以区分出两个电离，这两个电离与两个构象异构体a和b的烯丙基pi（C [双键] C）轨道有关，并且能量的差异在于DeltaIP（C [双键] C） 。备选地，可以通过比较各个具有相同取代基的酚和茴香醚的PE光谱来间接确定DeltaIP（C [双键] C）。发现在0.3和1.1eV之间的DeltaIP（C双键，长度为m-C）。通过IR光谱法测量CHCl 3溶液中OH振动的频移Deltanu（OH）。通过对分子内氢键强度，DeltaIP（C [双键] C），Deltanu（OH）值和取代基常数之间关系的相关分析，确定了4位取代基如
• Polyphosphazene process
  申请人：ETHYL CORPORATION

  公开号：EP0159020A2

  公开（公告）日：1985-10-23

  A process for making an alkali metal alkoxide (e.g. sodium alkoxide) of a halogen-substituted alcohol (e.g. fluorine-substituted alcohols) by dispersing an alkali metal (e.g. sodium) in a cycloalkane (e.g. cyclohexane) or a cycloalkane containing a phenol (e.g., o-allylphenol) and adding the resultant dispersion to an ether (e.g. THF) solution of a halogen-substituted alcohol. The resultant alkali metal haloalkoxide solution, or alkali metal haloalkoxide solution containing phenoxides, can be reacted with a phosphotnitrilic chloride polymer to introduce haloalkoxide substituents or haloalkoxide and phenoxide substituents.

  将碱金属（如钠）分散于环烷烃（如环己烷）或含有苯酚（如邻烯丙基苯酚）的环烷烃中，然后将分散液加入卤代醇的乙醚（如四氢呋喃）溶液中，制成卤代醇（如氟代醇）的碱金属碱氧化物（如碱氧化钠）的工艺。 所得碱金属卤氧化物溶液或含有苯氧基的碱金属卤氧化物溶液可与磷硝酰氯聚合物反应，以引入卤代醇取代基或卤代醇和苯氧基取代基。
• A Kinetic Study of the ortho-Claisen Rearrangement¹
  作者：Harlan L. Goering、Robert R. Jacobson

  DOI：10.1021/ja01546a024

  日期：1958.7
• Agonists and Antagonists of Antennal Responses of Gypsy Moth (Lymantria dispar) to the Pheromone (+)-Disparlure and Other Odorants
  作者：Erika Plettner、Regine Gries

  DOI：10.1021/jf904139e

  日期：2010.3.24

  Insects use the sense of smell to guide many behaviors that are important for their survival. The gypsy moth uses a pheromone to bring females and males together over long distances. Male moth antennae are equipped with innervated sensory hairs that selectively respond to pheromone components and other odors. Host plant odors, in particular, are detected by moths and sometimes cause an enhancement of the antennal and behavioral responses of the moths to their pheromone. Inspired by naturally occurring agonists and antagonists of insect pheromone responses, we have screened, by electroantennogram (EAG) recordings, a collection of compound sets and of individual compounds. We have detected interference of some compounds with the EAG responses of male gypsy moth antennae to the pheromone. We describe three activities: (1) short-term inhibition or enhancement of mixed compound + pheromone plumes, (2) long-term inhibition of pure pheromone plumes following a mixed compound 4-pheromone plume, and (3) inhibition of the recovery phase of mixed compound + pheromone plumes. Long-term inhibition was robust, decayed within 30 s, and correlated with the inhibition of recovery; for both activities clear structure-activity patterns were detected. The commercial repellent N,N-diethyltoluamide (DEET) was included for comparison. The most active and reproducible short-term inhibitor was a mixture of 1-allyl-2,4-dimethoxybenzene and 2-allyl-1,3-dimethoxybenzene. The most active long-term inhibitors were a set of 1-alkoxy-4-propoxybenzenes, DEET, and 1-ethoxy-4-propoxybenzene. DEET was more specific in the olfactory responses it inhibited than 1-ethoxy-4-propoxybenzene, and DEET did not inhibit recovery, whereas 1-ethoxy-4-propoxybenzene did. Target sites for the three activities are discussed.